3-O-乙酰基-4,6-O-苯亚甲基-D-葡萄糖醛 | 14125-71-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃二恶英
• 中文名称: 3-O-乙酰基-4,6-O-苯亚甲基-D-葡萄糖醛
• 英文名称: 3-O-acetyl-4,6-O-benzylidene-D-glucal
• 英文别名: [(4aR,8R,8aS)-2-phenyl-4,4a,8,8a-tetrahydropyrano[3,2-d][1,3]dioxin-8-yl] acetate
• CAS: 14125-71-4
• 化学式: C₁₅H₁₆O₅
• 分子量: 276.289
• InChiKey: OOUSBTQEYNLCKG-JKXDFHQYSA-N

物化性质

• 沸点：
  406.7±45.0 °C(Predicted)
• 密度：
  1.26±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-O-乙酰基-4,6-O-苯亚甲基-D-葡萄糖醛 在 silver(l) oxide 作用下， 反应 24.0h， 生成 (4aS,5R,8aS)-5-((4S,5R)-5-Hydroxy-2-phenyl-[1,3]dioxan-4-yl)-1,4-dioxo-1,5,8,8a-tetrahydro-4H-naphthalene-4a-carboxylic acid methyl ester
  参考文献：
  名称：

  生成的2-甲氧基羰基-醌与D-葡萄糖基二烯的狄尔斯-阿尔德反应：一种新的佛司可林方法

  摘要：

  2-甲氧基羰基-醌与基于葡萄糖的二烯（- ）的Diels-Alder反应以立体和区域特异性方式提供了-加合物（- ）。化学转化提供- 。化合物，并且是在毛喉素的合成提出关键中间体。

  DOI：

  10.1016/s0040-4039(00)99597-2
• 作为产物：
  描述：

  4,6-O-(苯基亚甲基)-D-吡喃葡萄糖三乙酸酯 在 bis(cyclopentadienyl)-titanium(III) chloride 作用下， 生成 3-O-乙酰基-4,6-O-苯亚甲基-D-葡萄糖醛
  参考文献：
  名称：

  Rapid Preparation of Variously Protected Glycals Using Titanium(III)

  摘要：

  Glycosyl chlorides and bromides can be rapidly converted to glycals in high yield by reaction with (Cp2Ti[III]Cl)(2). This reagent tolerates a wide range of common carbohydrate protecting groups, including silyl ethers, acetals, and esters; the methodology provides a general route for the preparation of glycals substituted with both acid- and base-labile functionality. A reaction mechanism is proposed that is based on heteroatom abstraction to give an intermediate glycosyl radical. This radical reacts with a second equivalent of Ti(III) to yield a glycosyltitanium(IV) species. P-Heteroatom elimination from the glycosyltitanium(IV) complex gives the glycal.

  DOI：

  10.1021/jo982447k

文献信息

• Nitro-polyols via Pyridine Promoted C═C Cleavage of 2-Nitroglycals. Application to the Synthesis of (−)-Hyacinthacine A1
  作者：Shengbiao Tang、De-Cai Xiong、Shende Jiang、Xin-Shan Ye

  DOI：10.1021/acs.orglett.5b03607

  日期：2016.2.5

  A mild and convenient transformation for the synthesis of nitro-polyols is described. The nitro-polyol derivatives were prepared either from 2-nitroglycals via a pyridine-promoted scission of the carbon–carbon double bond or from glycals via a sequential nitration–scission procedure. The generated nitro-polyols could undergo a stereoselective Michael addition reaction. The utility of the addition products

  描述了用于合成硝基多元醇的温和且方便的转化。硝基多元醇衍生物是由2-硝基糖类通过吡啶促进的碳-碳双键断裂或序贯硝化-断裂过程由糖类制备的。生成的硝基多元醇可能会发生立体选择性迈克尔加成反应。通过（-）-扁豆碱A1和7a- epi -（-）-扁豆碱A1的简明合成来举例说明添加产物的效用。
• Variously substituted glycals are readily prepared from glycosyl bromides using (Cp2TiCl)2
  作者：Roxanne P Spencer、Jeffrey Schwartz

  DOI：10.1016/0040-4039(96)00865-9

  日期：1996.6

  Glycosyl halides, variously substituted with ether, acetal, or ester protecting groups, were converted to the corresponding glycals in high yield by reaction with (Cp2TiCl)2. A glycosyl chloride was less reactive than the analogous bromide.

  通过与（C p2 TiCl）2反应，高产率地将被醚，缩醛或酯保护基不同取代的糖基卤化物转化为相应的糖基。糖基氯的反应性低于类似的溴化物。
• Selective formation of C-2 azidodeoxy-d-glucose derivatives from d-glucal precursors using the azidonitration reaction
  作者：Peter H. Seeberger、Susanne Roehrig、Peter Schell、Yuan Wang、William J. Christ

  DOI：10.1016/s0008-6215(00)00111-7

  日期：2000.8

  groups, were subjected to the azidonitration reaction to furnish the corresponding C-2 azidodeoxy-D-glucoses. 4,6-O-Isopropylidene-3-O-triisopropylsilyl-D-arabino-hex-1-enit ol afforded 2-azido-2-deoxy-4,6-O-isopropylidene-3-O-triisopropylsilyl-D-gluco pyranosyl nitrate and its D-manno isomer in a 20:1 ratio. These findings allow the azidonitration reaction to be now used for the preparation of a variety

  一系列由环缩醛保护基保护以构象地约束C-4和C-6羟基的葡聚糖进行叠氮化反应，以提供相应的C-2叠氮基-D-葡萄糖。4,6-O-异亚丙基-3-O-三异丙基甲硅烷基-D-阿拉伯-十六烷基-1-烯醇得到2-叠氮基-2-脱氧-4,6-O-异亚丙基-3-O-三异丙基甲硅烷基-D-葡萄糖硝酸吡喃酯及其D-甘露糖异构体的比例为20：1。这些发现使得叠氮基化反应现在可用于由受保护的葡糖前体制备各种葡糖胺结构单元。
• A Novel Aspect in Chlorination of D-Glucal Derivatives. Important Roles of the 4,6-<i>O</i>-Benzylidene Group and Substituent at<i>C</i>-3 in the Selective Formation of β-D-<i>Manno</i>and β-D-<i>Arabino</i>Isomers
  作者：Tohru Sakakibara、Takumi Yatabe、Kohji Yoshino、Yoshiharu Ishido

  DOI：10.1246/cl.1987.7

  日期：1987.1.5

  In contrast with the precedent reports described in peracetyl-and perbenzyl-D-glucal, chlorination of 3-O-acetyl- and 3-deoxy-4,6-O-benzylidene-D-glucal in carbon tetrachloride predominantly occurred from the β-side to give the β-D-manno and β-D-arabino adducts, respectively.

  与过乙酰基-和过苄基-D-glucal 中描述的先例报告相反，四氯化碳中 3-O-乙酰基-和 3-deoxy-4,6-O-benzylidene-D-glucal 的氯化主要发生在 β-侧分别给出β-D-甘露糖和β-D-阿拉伯加合物。
• Sc(OTf)3-catalyzed C-glycosidation of glycals: a facile synthesis of allyl glycosides, glycosyl cyanides and glycosyl azides
  作者：J.S Yadav、B.V.Subba Reddy、Pratap K Chand

  DOI：10.1016/s0040-4039(01)00629-3

  日期：2001.6

  The treatment of glycals with allyltrimethylsilane, trimethylsilyl cyanide and trimethylsilyl azide in the presence of catalytic amounts of Sc(OTf)(3) gave the corresponding 2,3-unsaturated allyl glycosides, glycosyl cyanides and glycosyl azides in excellent yields with high cl-selectivity. (C) 2001 Elsevier Science Ltd. All rights reserved.